James O'Keefe for Playboy

JANUARY 26, 2011

James O'Keefe is a conservative activist who likes to basically punk his way into the news. He was instrumental in taking down Acorn, and has tried to affect the public perception of Planned Parenthood through similar highjacks.

He overstepped his pranking when O'Keefe and three other conservative activists were arrested by the U.S. Marshals Service in New Orleans, Louisiana on January 25, 2010 on federalcharges of attempting to maliciously interfere with the office telephone system of Senator Landreau. Two of the activists had entered the federal building dressed as telephone repairmen, claiming they were responding to complaints that the phones were out of order.
He records people without their knowledge and does not represent who he is when doing so.
He's a goofball.
He also takes himself quite seriously for such a goofball and that explains this illustration for Playboy.

I was asked to paint him and show his distorted sense of self importance.
After placing him in recognizable paintings or images, a combo seemed to touch every base and I got to add the ridiculous touch of office chair wheels to that grandiose chair.

Some hope to become teachers, scientists, architects, chef or lawyers. James O'Keefe seeks to catch people off guard and if his usual hidden cameras or recording devices do their job, he will edit away the truth to tell the story he wants to tell.

Don't take this kid seriously. He's got that covered for you.

( this was edited. A previous version stated that he wiretapped the Landreau office. He was cleared of that charge.)

This would have of course been easier to paint and I think I was hoping to do this one, but I came to love the final. It felt more my own. Good lesson for me.

This is based on a photo of Lincoln. Just so perfect for his tall frame. It's a studied pose in a chair that needed to me mocked to work.

I almost always decide to show a client a revised sketch when we talk through a final idea. At first I thought it was over the top.

The final is much more rich than the sketch.

This is a zoomed in view of the painting. When I'm painting it I feel it's a loose painting. When it's reduced and printed or put on a site, it looks super tight. Story of my life.